This essay looks at the portrayal of women in Harold Pinter‘s plays Night School, The Lover and The Homecoming in an effort to analyse how they are portrayed and how they change from play to play. All three plays under discussion were written in the early 1960s and all deal with the double identity or split character roles of the woman. This portrayal of the duality of the woman is a recurring theme in Pinter‘s plays. Underneath various exteriors, many of his women reveal themselves to be sexually promiscuous yet without obvious censure from the playwright. I have therefore adopted the term “lovely whore” to describe this aspect of their character, the phrase Pinter uses as the final lines of The Lover. From 1960 to 1964, this character was rendered with more precision and focus in Pinter’s plays, accumulating into one of his most powerful characters, Ruth in The Homecoming. This coincides with the rise of the second wave of feminism, a social movement that focused on women‘s liberation and freedom of choice. During this time, Pinter explored the domestic, sexual and professional aspect of the woman, juxtaposing his female characters with male characters who struggle with the females in order to overpower them and inflict their will upon them. The character portraits rendered are of strong, independent women who prevail through conflict with the men in their lives and are able to retain their roles and harmonize them within their character. Although Pinter himself denied having a political agenda in writing these plays, they clearly deal with both gender and power within a domestic setting and subsequently carry a strong sexually political subtext. Thus, these three plays are marked by an attempt to resolve the issues that rose in the wake of the woman’s choice movement, and viewed in context, they render a feministic approach to the multiple roles of women and the men’s need to harmonize them in each character.